That Dexter Fowler is seeking a multi-year deal with an average annual value of $15-20 million is something that both he and the Cubs know and respect. That he would only stay a while, i.e. one more season, was an anticipated conclusion to Fowler’s stay with the Cubs when he returned, unexpectedly, in February. But every time we see his smile—and in his All-Star, World Series champion season, we saw that electric grin a lot—we cry a little inside, thinking of his contributions to the best Cubs team that any of us has ever seen.

The sentimental reasons for resigning Dexter Fowler are abundant and obvious. He’s become a fan favorite in only two seasons; he’s improved his defense greatly; and he’s the emblematic start of the Cubs’ insistent offense, the subject of the “you go, we go” ethos. Resigning him would make a wide swath of Cubs fans very happy, for purely emotional reasons, and that is a testament to Fowler’s considerable charisma and skill.

Of course, major-league teams do not commit tens of millions of dollars to retain players for sentimental reasons. They generally act in their self-interest, pursuing the best players for least money (emotions and ethics be damned), and the Cubs will do the same when weighing the decision to compete with other teams in the Fowler sweepstakes. And so…

Position: Center Field

2016 Stats: .276/.393/.447, .312 TAv, 3.7 WARP

How He Fits: The Cubs’ biggest question for 2017 is how the outfield is going to shake out. Declining Jason Hammel’s option eases the in-house fifth starter competition, and the bullpen will likely receive both supplementary help and a closer. The possible departure of Fowler, the maturation of Albert Almora, Jr., and the return of Kyle Schwarber all create an enigmatic outfield situation.

Resigning Fowler maintains the happy status quo. Schwarber slots in at left, Jason Heyward remains in right, and Almora and Jorge Soler (if the latter is not traded) get considerable playing time due to matchups and defensive optimization. Fowler’s two seasons with the Cubs have arguably been his best two, so they would be keeping a player who succeeds in the Cubs’ unique milieu. He’s socked 30 home runs, accumulated 7.4 WARP, and improved his defense while leading the Cubs to two NLCS appearances and a World Series championship.

Fowler fills two needs for the Cubs. Without him, they’re bereft of a leadoff hitter. If they don’t add another player, they probably tap Ben Zobrist as the leadoff man most days; his on-base skills, ability to see pitches, moderate power, and switch-hitting ability actually make him a fair comparison to Fowler.

That he plays center field makes Fowler a sensible reacquisition as well. While FRAA didn’t love Fowler’s 2016, the consensus is that Fowler played at least serviceably as he deepened his starting position. Almora is an excellent defender, but his hitting prowess is still somewhat unknown, which makes the young Cub less than a lock to claim the position. Heyward could be a better center fielder than even Fowler, and on par with Almora, but he hasn’t spent many innings there in his career. I speculated last offseason, immediately prior to Fowler’s surprise resigning, that Heyward would be a good center fielder, but that’s conjecture at this point.

We know why Fowler is good, having watched him play for two seasons. He hit a leadoff home run in Game Seven of the World Series, and he’s endeared himself to Cubs fans forever. He would be welcomed back warmly.

Why It Won’t Work: If the Cubs resign Fowler, they’re almost guaranteed to trade Soler. The five-outfielder configuration outlined in the above section guarantees that Ben Zobrist, Javier Baez, and Kris Bryant fight for only two spots on any given day, and both Joe Maddon and the front office will desire more playing time for Baez.

Essentially, the positional clog begins to actually be a problem. Multiple pieces will be on the move if Fowler returns, either for starting pitching or relief help. In that way, simple inertia is preventing Fowler from signing a contract with the Cubs.

Despite the reservations I listed about Almora above, the outfielder is a top-flight defensive player, and in that way the Cubs would actually improve. The team was historically good on that side of the ball in 2016, and they’re sure to regress, but Almora will appreciably improve the team’s outfield defense. Almora’s presence also makes Schwarber and Soler’s defensive inability more palatable. So, while Fowler is a good hitter and fine defender, the team’s overall health doesn’t suffer much with his departure.

Finally, and most importantly, Fowler is gonna get paid. Josh Reddick, the only outfielder to sign with a team already, got four years and $52 million with Houston, and Fowler is both a significantly better hitter and defender than Reddick. Fowler is second to only Yoenis Céspedes on the outfield market, and most predict he will get four or five years at $17 million average annual value.

Only six Cubs have set salaries for next season, totaling around $110 million. Many more are due for arbitration raises, some that might reach into the $10-20 million range. In a few years, Kris Bryant, Addison Russell, Javier Baez, Kyle Schwarber, Willson Contreras, and Kyle Hendricks will be due free agent contracts. It remains to be seen whether the Cubs will open the pocketbook for large free agent additions in the next few months, especially with Jake Arrieta’s impending free agency next offseason, but the organization will assuredly approach all prospective deals with caution.Alternatives: Ian Desmond headlines a thin centerfield free agency class, and the Cubs are significantly more likely to retain Fowler’s better defense and comparable bat than to spend on a converted infielder. Yoenis Céspedes and José Bautista are ill-fitting, $100 million contracts. Josh Reddick just signed with the Astros. Brett Gardner is rumored to be available via trade, but the Cubs would certainly rather spend money than prospects in getting a center fielder. Those factors considered, the most likely alternative is playing Almora and Heyward in center, with a corner outfielder added as depth.

Ultimately, I do not expect the Cubs to resign Fowler. If the exuberant outfielder gets 4/$70 million, however, the Cubs will have missed out on an opportunity to retain one of their top talents for an exceedingly reasonable price. Doubts about Fowler’s age (next year will be his age-31 season) are readily dismissed, considering his skill set: on-base prowess moderate power, and fairly good speed. Fowler is going to get a lot of money this winter, and rightfully so. “You go, we go,” Joe Maddon says; we’ll see whether Fowler stays or goes.

Zack is a history graduate of the University of Illinois, Urbana-Champaign, currently living in Boston. His writing has been published in Black Ball Journal, Cuban Baseball Legends: Baseball's Alternative Universe, and Baseball Prospectus. You can find his stranger thoughts at BP's Short Relief.